Trust of a friend who wishes to be more
by Heartless demon wolf
Summary: It has been six months since Eleanor had her heart broken by Theodore for falling in love with her sister Brittany. Can Alvin restore his friend's broken spirit? And more importently, her shattered heart?
1. A bet that should have never been made

**This is the sequal to Some question should never be asked. If you are not a fan of Alvin/Eleanor then please do not read, if you are then please read and review. This may be a two or three shot, have not decided yet, enjoy.**

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><p>Eleanor sighed loudly as she watched her fourteen year old green hooded wearing best friend Theodore Seville put his right paw around her pink clothes wearing sister Brittney Seville's shoulder as she giggled and snuggled into the arm that held her.<p>

It had been six months since Eleanor had expressed her love for Theodore with a few questions but he had completely misunderstood her topics and had flew with his heart out to her sister.

Now the two were together and she had to admit that while she was still heart broken the two did look like an honest, happy couple. They had their fights time and again but no one, human nor animal was perfect.

As the six chipmunks continued to walk to school, Eleanor could not help but notice the Alvin was starting at his brother Theodore and her sister Brittney with mild confusion as Eleanor rolled her eyes "Always the clue less one, eh Alvin?" she thought to herself with a smirk as Alvin caught Eleanor's eye then blushed before looking away making Eleanor blink as she felt a blush herself rise up to her cheeks.

"Wait. Why am I blushing over Alvin? I like Theodore...I always have...right?" she questioned herself before she was pulled from her thoughts by Jeanette who spoke out loud.

"I hope everyone remembered that today there is a spelling test in English today?" the blue clothes female chipmunk stated making all but her blue hooded wearing male counter part Simon groan in despair as both Alvin and Brittney turned their heads towards Jeanette.

"Wait, what TEST?" they shouted in unison making Theodore and Simon chuckle while Jeanette and Eleanor shook their head knowing that the two were hopeless losses.

"Britt, I warned you Friday before you and Theo went to the movies that we had a test and that you should study but you told me that you had it all taking care of" Jeanette answered glaring at her sister who smiled sheepishly and lightly slapped the back of Theodore's head with a paw when he snorted as he stared at her with wide innocent eyes making her only narrow her eyes at him as Simon continued Jeanette's annoyed rant but aimed it at Alvin.

"Alvin, you should have at least given Dave a better excuse then 'I'll do it as soon as this soccer game's over' when you and Ellie were watching TV last night" Simon sighed as he glared at Alvin who only shrugged with his paws in the pockets of his hooded.

"Hey, it got me out of doing my studying...and besides. Ellie's favorite team was on last night so I had to be there to support her if they won or lost" Alvin replied with a smile as Eleanor lightly blushed before she stuck her tongue out at him.

"But unlike you, I really did study. And I have a feeling that I will get an A, or at least a C if it comes down to it" Eleanor said with a smirk as Theodore's head dropped with a sigh.

"Well at least you three got to study, I was trying my best to understand what I was looking at but I fell asleep then woke up and had to make dinner...plus for the last two days I was a bit...preoccupied" he spoke with a small grin and his tail waving slowly behind him as Alvin scoffed.

"Theo, being with your girlfriend is not truly an excuse not to study for a test" Alvin said making all five animals stop in their tracks and stare at him with wide eyes like he had black and white striped fur all of the sudden.

"What? Why are you all staring at me like I have two heads? Starting to get a bit creepy" Alvin asked, his voice sounded worried and annoyed.

"Who are you and when did you kidnap our brother Alvin? Theodore shouted taking a step towards the red hooded wearing male chipmunk that was caught off guard by his younger brother's display of violence, if one could call it such.

"Face it Alvin, you and school work going together is like Simon dressing up and acting like a gangster...it just does not happen that way, as it should be" Eleanor replied making Alvin gasp.

"Who in the fur said I wanted to get taught anything from the brain washing factory? All I said was that Theodore could have studied a bit before going off with Brittney...he's not all that great at getting questions right you know" Alvin whispered to all but Theodore and forgot that they were chip mucks so they had really good hearing.

"At least I have a girlfriend, I do not see you doing anything in your spare time but look at yourself in the mirror and sing about how handsome you are that the world should fall in love with you" Theodore spat back making the group all but Theodore who crossed his arms over his chest with a smirk and Alvin whose jaw had almost dropped to the floor gasp.

"Ouch, that was a burn" Simon said with a small smile as Jeanette rolled her eyes and pushed Simon ahead of the rest while Brittney looked over her shoulder and with a kiss on Theodore's right cheek she spoke softly.

"Good for you, Teddy" before running towards her sister and her boyfriend as they carried on to middle school leaving Eleanor glancing back and forth between her friends.

Alvin, who still had his mouth open in shock closed it to look at his now smug green hooded brother who slowly frowned and uncrossed his arms as Alvin spoke "So what are you saying, Theodore? You don't think I can get a girlfriend, is that it?" he asked puffing out his chest as Theodore sighed, his once in a lifetime prideful nature and comment gone as he blinked and replied.

"No, Al. I did not say that...all I meant was that instead of always trying to brag that you got or could get a girl...you go and talk and get to know one THEN you become, well...mates, I guess" he said softly, Alvin frowned, not used to getting advice from his baby brother of all people, or animals.

"Huh...you know, Theo. You could be right" Alvin spoke making both green wearing animals glance at him in surprise.

"I am?"

"He is?" both chipmunks replied in unison as Alvin nodded, a bit annoyed that everything he seemed to say came as a shock to his friends and family.

"Yes" he said as he raised an eyebrow at the two, or would if he had any and continued.

"I'm going to do my best to find myself the girl of my dreams...and your going to help me, Ellie" Alvin ordered as Eleanor opened her mouth in surprise and without neither of the two knowing, she blushed.


	2. Partner in crime or love

**I'll be honest and say this chapter is short...but you already know that. Also, I did not know what to really put, next chapter will be better though. If anyone got any ideas, I'll be glad to do them, thanks.**

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><p>Eleanor felt her jaw drop as Alvin put his books inside his locker, her mind still not catching up with the 'bet' that had been made with Alvin and Theodore, her best friend. The three had got to school on time and Theodore had ran to kiss Brittney good bye before she went off with her cheerleader friends and he went to breakfast that he did not get because he's been trying to go on a diet, which did not do him much justice. Simon and Jeanette had gone stright to class as Alvin had gone to his locker and Eleanor had obviously followed him.<p>

"Hold on, I in no way want to be a part of this...Al, you can get a girlfriend by yourself. Why would you need my help?" Eleanor asked blinking as her eyes narrowed in anger before Alvin put his paws on her shoulders.

"Ellie, please, I know I'm labeled as 'the player' and I'll admit that I do sometimes flirt with girls" he chuckled with a paw rubbing the back of his head as Eleanor crossed her arms over her chest and narrowed her eyes to mere slits making Alvin suddenly ashamed of disapproving the blond haired chipmunk in front of him.

"But, since when I you ever seen me on a date with any of those girls? A human and a chipmunk, someone better call P.E.T.A" he added with a nervous grin making Eleanor roll her eyes at him.  
>"What about Brittney? I been told that you two were supposed to be the 'cool' couple" Eleanor spat as it was Alvin's turn to roll his eyes.<p>

"Come on, Ellie. Not everyone is perfect for another person, I mean Brittney is beautiful and has a gentle, caring side...somewhere where her heart is supposed to be" he shrugged and shook his head as Eleanor curled in paws in anger and swiftly added before she could yell at him, or worse.

"But...she's not my type, and you seen for yourself the passion that she and Theo have for one another...it's like trying to tear away the love of two soul mates, it just does not happen. Heh, even Simon's got more game then me when it comes to girls...wow, never thought I would say that. I must be sick or something" Alvin spoke with a frown and a paw on his forehead as Eleanor had a large grin on her face, her arms still crossed over her chest as she replied.

"Not your type huh, Rock star? Well then, if I really have to help you find a girlfriend then you must tell me everything that you would like in a women" she said smugly as Alvin rolled his eyes and was about to reply when the school bell rung, signaling that the day for learning had begun.

"Talk to you at lunch, Chef" Alvin laughed with a smile as he ran to his classroom with his small backpack, waving a paw and his tail as he disappeared into the crowd.

"Chef, is that supposed to be a new nickname for me?" Eleanor thought slowly as she slowly smiled then shook her head; this was going to be journey that she did not want to forget, anytime soon.  
>After a class of culinary arts that Eleanor had with Theodore in which he had talked about a volleyball game that the six played last Sunday and how Alvin had got caught in the net making Eleanor chuckle at the memory she thought in more detail about Alvin.<p>

How he can be so full of himself yet so caring when it came to family and sometimes friends, how he always creates some scheme to get his brothers and sometimes the chipettes in trouble but can always be there when another was in trouble or needed help, and at last how even though he tried to hog the stage when singing, he allowed the others their fair share.

Not to mention that he was on handsome looking boy, with his brown, chestnut colored fur, his amber colored eyes and his toned tight six pack of abs. Alvin may not have been the perfect male animal for someone like Eleanor but she could not help but slowly wonder.

"Do I honestly want some other female animal or not to steal...my crush?" she asked herself before being torn away from her thoughts by the bell to lunch as she blushed, embarrassed to be caught slightly drooling about a boy who may not even want her.

With a sigh at her confused emotions, Eleanor walked to lunch, wondering if she wanted to help Alvin Seville get a girlfriend for him, when she just may be the girl he was looking for all along. She just needed to know if he was the one she wanted...maybe time would tell.


	3. Choices are never easy

**Sorry this is short everyone, I been busy with work and playing video games in my spare time. I won't give up on my stories that I like, such as this one, so expect another update either tomorrow or somtime next week but it will get done. Meanwhile would anyone mind throwing me a cute idea for the pair please? I'm running out right now. Read and review, peace.**

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><p>"Well...how about Vanessa?" Alvin asked slowly while putting a thin French fry in his mouth and chewing as he thought carefully making the other five chipmunks shake their head at him as he swallowed.<p>

The six were at lunch in school, standing on a tan colored table and for now...trying to find the right...mate for Alvin, the 'bet' that Alvin and Theodore made was that Alvin 'the awesome one' Seville had to find a...mate or girlfriend in human terms within three weeks.

If not then Alvin had to give Theodore his allowance and record money for a month and two solos of Alvin's were to be given to Theodore. If Alvin won, then not only would he get an animal girlfriend, but Theodore's record money and two solos of Theodore's as well, which they both thought was fair.

Eleanor and the others thought it was a stupid bet and had the cause of breaking or repairing a female's heart, but Alvin had been making Theodore do some really embarrassing and stupid things over the years, they felt he was entitled to a little payback...in the only cute, innocent fashion he knew how.

Ever since the chipmunks had come to high school other talking animals had followed, making the stars more friends...as well as enemies.

Vanessa Campbell was a black and white striped female skunk with green eyes that had a really high pitched annoying voice and could never help but cause trouble. Or pain to others, even when it was not truly her fault.

"Al...you know for a fact that Vanessa is not your type...she's a member of the debate team, granted you love to argue but you already blown her off at least a dozen times...plus she has a large pimple on her chin, and drooling problems from what I heard" Simon replied making everyone even himself shiver before Brittney rolled her eyes and leaned to the side against Theodore's right arm which was trying to reach for a paw full of Cheetos causing the young, large and shy chipmunk to frown before shrugging and putting his right arm around his mate who smiled in content.

Alvin glanced at the young couple then turned towards Eleanor who was eating a red apple while trying to keep her napkins from flying into the air with her tail, causing Alvin to chuckle "She's just so cute when she tries to do things on her own" Alvin thought before shaking his head to clear his thoughts which seemed to do the opposite.

"Wow...did I just think Ellie as being...cute?" he blinked while wondering before Jeanette cleared her throat looking at Eleanor blinking then looking at Simon who had just got done with his lunch and was staring at Theodore and Brittney who were giggling with their heads close to each other.

Simon shook his head, deciding not to bother the two love munks before getting his small tray and throwing the contents away in the garbage turning to Alvin before Jeanette did the same and was waiting for him so they could move to their next class together.

"Alvin...whoever this special 'mate' for you is...I just hope they make you see that love is not just fun and games, alright brother?" he said softly forcing Alvin to tear his gaze away from Eleanor who had finished her apple and was now drinking her milk with a straw.

Alvin, feeling his heartbeat speed up in...nervousness nodded at his brother "I understand, Si…thank you" he spoke with honesty causing the smart chipmunk to open his mouth in surprise before it closed and his eyes narrowed in suspicion.

"I sure hope so" Simon whispered allowing Alvin and Eleanor to eat their lunch as the two wise, blue colored chipmunks went towards their next class which was math.

Theodore with one paw on his tray and one arm around his mate threw away his tray, waved his tail goodbye for Eleanor and Alvin and escorted Brittney to her next class, leaving the two alone.

Alvin rubbed the back of his neck fur with a paw looking at Eleanor who raised an eye brow at him...but then remembered that they did not have any...being chipmunks. Drinking the last of her milk, Eleanor looked around and saw all types of different animals hanging around humans and speaking with them as she softly chuckled.

"What has the animal kingdom come to?" she thought before hearing the bell ring, telling all that lunch was over and it was time for Alvin's and Eleanor's next class together which was gym and their favorite because of soccer.

Eleanor hoped that she could help Alvin find real love within the three week time period. She really did.


	4. Earth angel with fur

**Thanks to some encouragement from an author friend, I decided to update this story, as promised but with more…..style. I love this pair as it's my second favorite. Even though I despise Alvin, anyway I'm hoping to get an idea or two about where you would like the couple to do or where to go, but rest assure that I will not derail from the original plot in mind, thank you and read and review please.**

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><p>Eleanor slowly looked up and taking a deep breath opened the door to gym, stepping inside where thirty students and the gym teacher plus Alvin who wore a red gym t-shirt which did not cover his tail and grinned at her was waiting, making Eleanor smile then blush lightly.<p>

"Why do I keep doing this to myself, I'm supposed to help him find a girlfriend. Not fall in l...wait, WHAT?" she shouted to herself jumping into the air when the coach blew her whistle.

"Alright everyone, listen up. I want all of you to run a mile then get outside so we can play soccer" the brown haired, green eyed women who looked in her thirties spoke calmly as the students cheered then replied respectfully.

"Yes Mrs. Leon" before they did as ordered, ignoring the two eleven inch chipmunks jogging by their side and behind them as the humans had longer legs, the chipmunks running on all four paws at a slower pace.

"You seemed nervous, Ellie, everything ok?" Alvin asked confused keeping up with his sports partner as she rolled her eyes trying to come up with an excuse to not blush or look into his amber colored eyes as she merely replied.

"I had to use the restroom after lunch" which stopped any other vocal conversation until every student got outside into the green grass field with its steel gray colored bleachers and clear blue with shining sun sky above them. Alvin breathed in a large breath of oxygen, smelling the freshly cut grass and pine trees around them before exhaling with a loud sigh of content causing Eleanor to do the same and softly speaking.

"It's a really beautiful day out" she commented slowly making Alvin chuckle and nodding before saying without thinking his words through.

"Your even more beautiful" he said out loud forcing Eleanor to look over at him in surprise and a hint of a blush as Alvin cursed before quickly replying.

"I…I uh mean that this day could not get any more perfect" he strutted clearing his throat waiting for Eleanor's words as she swallowed the spittle in her throat and calmly said.

"Only if you have the right person to spend it with, eh Alvin?" allowing him to nod and sigh in relief not seeing the smile on Eleanor's face or catching her romantic hint before he looked up and paused, loving the way the sun reflected off her blond pigtails, furry face and tail which was not hidden by the small light green gym shirt she wore as she blushed heavily then grinned "Hey Alvin?" she whispered softly making Alvin answer with a simple.

"Huh?" before Eleanor used her left paw to touch Alvin's left cheek gently who blushed and started at her with a small hint of lust in his eyes as she whispered into his ear.

"We should get out onto the felid now, don't you think?" she spoke before laughing and running onto the field in front of her, leaving a dumbstruck Alvin all alone as he blinked slowly then he brain kicked into high gear before he spoke one word.

"Oh" before running to catch up to his childhood friend as he shook his head, not believing that she tricked him. He was going to get her for that, her tan colored fur, her plump but soft hips and her puppy like expression with her emerald green eyes that melted his heart when she looked at him. She was like an angel...only with fur and a tail...maybe he should forget the dumb b-

Alvin's train of thought was cut off suddenly as he ran into a tree at full speed before rebounding off of it in pain, causing all the students but Eleanor and Mrs. Leon to laugh so hard they cried as Alvin held his injured forehead but quickly came to and ran back to the group of students glaring at the blond, furry beauty who only shrugged and chuckled knowing he would not let a tree wound his ego.

He was going to get her back alright, for stealing his heart...but he would have to make a trap that only a master like himself could create and it would take time. But it was trap that would be well worth it, for a blond angel like she would not be easy to take for himself.


	5. Suspicions from the smart one

**Disclamer: I do not own Alvin and the chipmunks for well...you know. any way, enjoy!**

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><p>Alvin could not believe his bad luck as he looked in the mirror, behind him Theodore and Simon were laughing and by laughing it means that they were on the floor crying thier eyes out in laughter as they clutched their sides and tried to get oxygen back into their lungs but were failing...badly.<p>

Alvin scowled looking at his younger brothers in the mirror then smiled when Theodore started coughing for a few seconds then took a few deep breaths, chuckled, looked up at Alvin and started laughing very hard all over again making the red sweater wearing chipmunk with amber colored eyes growl and muttered something that could not be heard under his breath.

Eleanor cleared her throat before whacking both Theodore and Simon with a wooden spoon on their rear that she just...happened to have. "Stop laughing you two, it's not that funny, Alvin looks great and you two should support him as your brother" Eleanor said with her eyes narrowed at the two and her arms crossed over her chest waiting for the two brothers to catch their breaths and speak.

"W...we are supportive…at least in telling him that he has bad taste in clothing!" Simon spoke shouting the last word making the two laughs their tails off all over again as Eleanor glanced over to the self-conscious older male chipmunk who groaned sadly causing Eleanor to frown as Alvin wore a red shirt sleeve jacket with gray shorts and a very small chain necklace.

Eleanor did not understand what his brothers problems were, he did not look that bad Eleanor herself, even though he could lose the shorts because he had fur to cover any...private parts. But over all she did not know why the two brothers were making such a big deal over him, she herself would even say that he was handsome, with the fur on his head slicked back.

Now all he needed with a pipe and maybe he would look like a grandpa in the 1940's. The thought caused Eleanor to quietly giggle, but then blush softly as she thought of growing old with Alvin Seville by her side, and thought...that maybe it would not be so bad if she gave him a chance.

Tuning out of her day dream, Eleanor scowled and smacked the two brothers who were still laughing on the floor of the chipettes house as they stopped and rubbed their rears in pain.

"That hurts you know, Ellie" Theodore commented as she only stuck her tongue out at him like a child before replying.

"Good, maybe next time the two of you would not be so harsh to Alvin the next time your forced...I mean asked to wear clothes that might impress a lady" she said before looking to her right where Jeanette was rubbing her head with her two front paws and her eyes closed as Brittany had her eyes narrowed at the two brothers then rolled in annoyance when Theodore winked at his mate.

"Finally...they stopped, after ten minutes. I had half a mind to beat you both till your fur was black and blue" Jeanette sighed loudly forcing Simon to retort with.

"I think you mean until our fur was, OW-" he hissed as a wooden spoon was thrown at him and hit him in the nose making him rub it before glaring at Brittany who high fived her sister, as she was the one to steal the spoon and throw it at the blue sweater wearing male chipmunk.

"You ma'am has a nasty attitude" he growled making Theodore glare at him but did not speak then ducked as another wooden spoon flew at Simon hitting him in the shoulder making the chipmunk shout loud in pain, this one being thrown by Jeanette who high fived both her sisters.

"Look...we did not bring you two here to mock your brother and cuddle with us...even those there is nothing wrong with that. I have worked hard on making this jacket and shorts not to mention that I had to have Theodore pay quite a bit of money on the necklace...the bet will end next Friday, and Alvin has only been on three dates. One with a female robin, one with a female gray furred fox and one with for some strange reason that I will never understand...a female bat.

And he has yet to choose any of them never mind calling them back or asking for a second date...Al, I love you like a brother but you have to pick a animal, otherwise you may be alone for the rest of your life" Brittany said softly, catching her breath and causing the male to look at her then take a deep breath before exhaling with a nod.

"I know, Britt...but it's just hard...the girls that I date only really like me because I play sports and am a MAJOR ROCK STAR!" he shouted the last words before playing air guitar making all five animals present to roll their eyes.

"Besides...they just don't seem to be my...type" Alvin added quietly with a serious tone making all but Simon look at him in confusion, Simon only having a bored expression on his face as he got up and stood beside Jeanette.

"Really...so what DO you want in a female or mate, Al?" Theodore asked slowly getting off the floor and taking a cap of water that Eleanor held out for him then drank with a nod to her before jumping in pain and surprise, spilling the water as Eleanor hit him in the rear with another wooden spoon that she held in her paws, causing Theodore to wonder just where she got all these wooden spoons from, then turned to Alvin as he answered Theodore's question.

"I...I want a girl that had the same in common with me. The same music, can be loyal to me while understanding that sometimes we need space for a while, and who can be almost as great as I am in sports...someone who likes me for myself rather than my fame or title in school" Alvin replied looking into the mirror at his appearance then quickly glancing at Eleanor before shifting his eyes to everyone eyes who was starting at him with different expressions on their faces.

Jeanette put her right paw to her chin while she thought to herself slowly, Alvin had been through dating hell with that the animal females in school, even some human females who wanted to date him but he gently refused. As she watched him be with different girls she realized that he looked...disappointed, which was not like him.

He would normally be cheerful and bragging about one thing or another but throughout the whole three almost four weeks of the 'bet' he had never once even called any of the girls back or given them a kiss goodnight according to Simon, who told her what Alvin had told him of his 'dates'.

As far as Jeanette was concerned, Alvin did not even like any of the females that he had dated, braking up with them only a day or two later, which confused her even more. There were some very beautiful animal females who rivaled even Brittany in that aspect, not that she herself would agree.

Why did he only go to the ones that he had nothing in common with...what was he trying to prove, and more importantly, why did he always go to Eleanor for help with something he could do with no trouble at all himself.  
>Suddenly Jeanette, being the smart although she was clumsy chipmunk mind clicked as she figured out the only answer that made sense...Alvin had a crush on her baby sister, Eleanor.<p>

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><p><strong>And this is where we put the word known as EPIC FAIL for Alvin, not so much for Eleanor though, hope you like it so far.<strong>


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